Got my 1927 DT2 250 running well! What seemed to have made the most difference was changing out the contact breaker assembly in the flywheel. I was getting a much healthier spark after doing that and the bike starts up within 1-3 kicks now.Some additional questions as I continue working on the bike.

Oil Leaks
1. Theres 2 bolt plugs at the bottom, the one on the right (oil pump side) I know I can drain the transmission oil from. Will undoing the bolt on the left (flywheel side) drain the same oil reservoir?I'll be looking to replace the gasket for both plugs. 

2. Also there’s a slow oil leak on the left side which seems to be mixed with dirt or metal? I think this is seeping from old plugs where the clutch cable meets the push rod, which I hope isn’t ground metal, mixed with oil. Or is the discoloration coming from the oil/dirt picked up by the chain? Any thoughts on whether this is indicative of the clutch plates or push rod needing to be cleaned or replaced?

3. There seems to be a slow oil leak coming from where the cylinder meets the exhaust pipe. Is this normal or do I need to adjust the oil pump to feed less oil? I also haven’t installed the gasket thread mentioned in the parts manual (248-14623-00-00) could that be the cause?
 
Electrical
1. My headlamp, tail light and front turn signals all work, but the rear indicator lights won’t turn on. I have the wires connected correctly (green to green and brown to brown) not sure if its missing a ground somewhere?

2. The front turn signal lights turn on, but they won’t blink, which I’m pretty sure is related to the flasher relay? When I initiate the turn signal switch, I can hear the flasher relay click 3 times. But nothing happens. Is the flasher relay bad or do the tail lights need to be connected correctly first for the flasher relay to work properly? 

General Questions
1. Should this bike be able to get to 5th gear? It seems to only go to 4th and I’m maxing out around 50/55 mph. 

I really appreciate all of the help I’ve received from this community that's allowed me get to this point!This is my first motorcycle and I’ve gone from knowing absolutely nothing about motorcycles to being able to get this one running, with the help of the community and information in this forum.


 

Lets talk about the worst sounding problem first.
If no 5th gear then we have a problem.
Tell us more please. Is there an indication of trying to hook a gear etc--what happens if anything.
Left [call it a drain bolt --but not] undeneath houses the selector drum plunger & spring.
If you've had it out [sounds like not] then look in the oil tray for plunger & spring but the gearchange would feel 'all up the creek' without those items in place.
Drain bolt is the next one over but both would drain it regardless if mistakenly removed.
Not sure if your oil leaks are much to worry about just yet. Sounds like pushrod seal on the left, could be chain throwing oil, could be sprocket nut not tight & seeping oil then getting on the chain then throwing it. If ya worried clean it off & check again after a ride.
Not sure about tail light but i'm guessing brown powers it if [battery powered] & green sounds like green/yellow for brake light].
But if i'm wrong [again] & you're talking green & brown are you talking dark green & dark brown [which are blinkers] so is there a clue there.
But if you have it wired correect & missing the black to earth you could check just by jumping a wire from the bulb socket with lense off & run it to the frame--anywhere that earths out.
I'm in NZ so all our tail lights i think would be blue as magneto powered with the instruments--& headlight in a roundabout way.
Ok looks like i read your story wrong--Tail light works but rear indicators don't. Maybe ignore half of my rant above or pick out anything usefull.
Indicators need an earth or if solidly earthed to the frame they should work. Need an earth if rubber mounted though.
Here's a link to a wiring diagram [not color] but shows blue to tail like ours so--i don't know--but shows earths at blinkers [indicators--flashers wherever you are].
Man i hate wiring diagrams sorry & i get lost. No color but are named for colors i see.
Blinkers on yours at the rear might have an earth terminal that fits on the blinker stalk thread plugging to any black back there & should be black with double connectors there spare if that's the case.
Now i've totaly confused everything i'll let someone sot it out [me out lol].
Defo a 1972 DT2?, had one new but that's another story.
www.thumpertalk.com/forums/topic/1255071...-dt2-ignition-wires/

Congrats on getting your bike running good! I will take a run at a couple of your issues. My bike is a 73, DT3, very similar to yours except in front wheel size and paint color, I believe. I got it last October and have sorted through quite a few minor issues this Spring.
Oil leaks - I had a nagging oil leak that took me quite a while to pinpoint. I replaced both gaskets on the bottom. As RT325 points out, when you take out the one closest to the shift lever, a spring and a piece of metal will fall out. Not a big deal, just put back in the same way, good to go. I eventually figured out that my oil leak was coming from the air inlet hose for the injection oil tank. This hose goes into a hole on the left side, just above the chain. I was topping off the injector oil, which led to the oil overflowing thru this hose everytime I went for a ride. I ended up capping off the fitting at the tank and putting a threaded 1/4" elbow fitting in the oil injection tank cap. No more leak. You can still buy new oil caps, which I did because I didn't want to drill out my 50-year old cap (set it aside for originality).
When I first got my bike I also had no tail light or rear brake light (same except for which filament lights). I have blue, yellow, and black wires coming from mine. Through trial and error figured out that the black wire wasn't grounding. My bike does not have turn signals so I used one of the turn signal ground wires and it works great. It sounds like you need to find or put in a ground wire somehow.
Hope this helps a little.
Good luck!

Oil leak #2 could be the push rod seal, and #3 could be a head gasket. Because of the angle of the cylinder, head gaskets will tend to drip down the exhaust side.